Methyl p-toluenesulfonate → 5-Chloro-2-methyl-3-phenylisoindole-1-carboxylic acid [3-(2-methyl-1,3-dioxolan-2-yl)-propyl]amide

HRID 1863091노트

반응식

HRID 1863091 반응식
[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][NH:10][C:11]([C:13]2[NH:14][C:15]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:16]3[C:21]=2[CH:20]=[CH:19][C:18]([Cl:22])=[CH:17]3)=[O:12])[O:6][CH2:5][CH2:4][O:3]1.[Na].[CH3:30]OS(C1C=CC(C)=CC=1)(=O)=O>CN(C)C=O.CO>[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][NH:10][C:11]([C:13]2[N:14]([CH3:30])[C:15]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[C:16]3[C:21]=2[CH:20]=[CH:19][C:18]([Cl:22])=[CH:17]3)=[O:12])[O:3][CH2:4][CH2:5][O:6]1

참가 물질

6

반응물 3

HCID 6645Methyl p-toluenesulfonateHCID 5360545SodiumHCID 543664105-Chloro-3-phenylisoindole-1-carboxylic acid [3-(2-methyl-1,3-dioxolan-2-yl)-propyl]amide

생성물 1

HCID 538171005-Chloro-2-methyl-3-phenylisoindole-1-carboxylic acid [3-(2-methyl-1,3-dioxolan-2-yl)-propyl]amide

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매2회

실험 절차

A solution of 24.0 g. of 5-chloro-3-phenylisoindole-1-carboxylic acid [3-(2-methyl-1,3-dioxolan-2-yl)-propyl]amide in 160 ml. of dimethylformamide is treated under an atmosphere of argon at 0°-5° C. with a solution of 2.1 g. of sodium in 40 ml. of methanol. The mixture is then stirred at room temperature for 30 minutes and subsequently added dropwise to a solution of 18.6 g. of p-toluenesulfonic acid methyl ester in 20 ml. of dimethylformamide. The mixture is subsequently stirred at room temperature for 30 minutes and then at 80° C. for 1 hour. After cooling, the mixture is poured on to 400 ml. of ice-water and, after the addition of 20 g. of sodium chloride, the separated product is removed by filtration under suction, washed with water and then dissolved in methylene chloride. The organic phase is washed with water, dried over sodium sulfate and evaporated to dryness. The residue obtained is chromatographed on 500 g. of silica gel using methylene chloride/ethyl acetate (4:1) for the elution. The uniform fractions are combined and evaporated, and there is obtained 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid [3-(2-methyl-1,3-dioxolan-2-yl)-propyl]amide having a melting point of 137°-139° C. Recrystallization from ethanol yields colorless crystals of the same melting point.

후처리

  1. additionsubsequently added dropwise to a solution of 18.6 g
  2. stirringThe mixture is subsequently stirred at room temperature for 30 minutes
  3. waitat 80° C. for 1 hour
  4. temperatureAfter cooling
  5. additionthe mixture is poured on to 400 ml
  6. customof sodium chloride, the separated product is removed by filtration under suction
  7. washwashed with water
  8. dissolutiondissolved in methylene chloride
  9. washThe organic phase is washed with water
  10. dry with materialdried over sodium sulfate
  11. customevaporated to dryness
  12. customThe residue obtained
  13. customis chromatographed on 500 g
  14. washfor the elution
  15. customevaporated

출처 및 근거

ORD 기록
ord-ca7ad2892d874692baa87ee88035c235
출처 데이터셋
uspto-grants-1979_09
특허 번호
US04167632

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